Adhesive composition

Abstract

Disclosed is an adhesive composition comprising (a) 100 parts by weight of a monomer mixture comprising a vinyl monomer having an acidic group in the molecule and a vinyl monomer copolymerizable with said vinyl monomer, (b) 10 to 500 parts by weight of a filler, (c) 0.01 to 10 parts by weight of a polymerization initiator and (d) 0.01 to 10 parts by weight of ascorbic acid or a derivative thereof. This adhesive composition has a high bonding force and an excellent durability even in a severe environment, for example, in the environment in the oral cavity. Accordingly, this adhesive composition is especially valuable used as a dental adhesive.

We claim: 
     
       1. An adhesive composition comprising (a) 100 parts by weight of a monomer mixture comprising a vinyl monomer having an acidic group in the molecule represented by the following formula: ##STR3## wherein R 1  stands for a hydrogen atom or a methyl group, and n is a number of from 4 to 12, and a vinyl monomer copolymerizable with said vinyl monomer, (b) 10 to 500 parts by weight of a filler, (c) 0.01 to 10 parts by weight of a polymerization initiator and (d) 0.01 to 100 parts by weight of ascorbic acid or a derivative thereof.   
     
     
       2. An adhesive composition comprising (a) 100 parts by weight of a monomer mixture comprising a vinyl monomer having an acidic group in the molecule represented by the following formula: ##STR4## wherein R 2  stands for a hydrogen atom or a methyl group, m is a number of from 2 to 4, and X stands for ##STR5## and a vinyl monomer copolymerizable with said vinyl monomer, (b) 10 to 500 parts by weight of a filler, (c) 0.01 to 10 parts by weight of a polymerization initiator and (d) 0.01 to 10 parts by weight of ascorbic acid or a derivative thereof. 
     
     
       3. An adhesive resin composition of a two-pack system comprising (i) a liquid component comprising a vinyl monomer having an acidic group in the molecule, which is selected from the group consisting of a monomer represented by the following formula: ##STR6## wherein R 1  stands for a hydrogen atom or a methyl group, and n is a number of from 4 to 12, and a monomer represented by the following formula: ##STR7## wherein R 2  stands for a hydrogen atom or a methyl group, m is a number of from 2 to 4, and X stands for ##STR8## or a monomer mixture of said acidic group-containing vinyl monomer and a vinyl monomer copolymerizable therewith and (ii) a powder component comprising ascorbic acid or a derivative thereof and a filler, wherein the components (i) and (ii) are filled in different packs and, at the time of curing, appropriate amounts of the liquid and powder components are taken out from the packs and are mixed.   
     
     
       4. An adhesive composition as set forth in claim 1 or 2, wherein the content of the vinyl monomer having an acidic group in the monomer mixture is 1 to 90% by weight. 
     
     
       5. An adhesive composition as set forth in claim 1 or 2, wherein the copolymerizable vinyl monomer is an acrylic acid ester or a methacrylic acid ester. 
     
     
       6. An adhesive composition as set forth in claim 1 or 2, wherein the filler is a homopolymer or copolymer of an acrylic acid ester or a methacrylic acid ester. 
     
     
       7. An adhesive composition as set forth in claim 1 or 2, wherein the polymerization initiator is at least one member selected from the group consisting of organic peroxides and tertiary amines. 
     
     
       8. An adhesive composition as set forth in claim 6, wherein the organic peroxide is a diacyl peroxide. 
     
     
       9. An adhesive composition as set forth in claim 4, wherein the content of the vinyl monomer having an acidic group in the monomer mixture is 1 to 50% by weight. 
     
     
       10. An adhesive composition as set forth in claim 1 or 2, wherein said filler has a particle size of 0.01 to 500 μm. 
     
     
       11. An adhesive composition as set forth in claim 10, wherein said filler has a particle size of 0.01 to 200 μm. 
     
     
       12. An adhesive composition as set forth in claim 1 or 2, wherein said polymerization initiator comprises a mixture of an organic peroxide and a tertiary amine. 
     
     
       13. An adhesive composition as set forth in claim 1 or 2, wherein said polymerization initiator comprises a mixture of an organic peroxide and an α-diketone. 
     
     
       14. An adhesive composition as set forth in claim 1 or 2, wherein said ascorbic acid is selected from the group consisting of L-ascorbic acid, D-iso-ascorbic acid and dehydroascorbic acid. 
     
     
       15. An adhesive composition as set forth in claim 1 or 2, wherein said ascorbic acid derivative is selected from the group consisting of metal salts thereof and esters thereof.